The Art of Being Friends With Your Boss Without Crossing Any Lines

That line between being manager and employee and buddy-buddy is a tricky one to navigate. You don’t want to be too buttoned up, but you don’t want to color too far outside the lines either. You want to have a great relationship with your supervisor, but you don't want to forget about the ever-present asymmetry of power. So how do you walk the tightrope of being friendly with your boss while stopping short of being close pals?

1. Leave the Crazier, Most NSFW Parts Out

You know that moment when everyone is gathered around the coffeemaker, hoping that third cup will do the trick. One colleague mentions the party he went to on Friday night; another one talks about the new guy she’s seeing. Sharing the escapades of your weekend is fine with co-workers who are also good friends, but your boss doesn’t need to be regaled with tales of your crazy Saturday night, no matter how friendly the two of you are.

A key component of any great employee is strong judgment. Everyone makes mistakes sometimes or does things he might not choose not to repeat if given a do-over, and if those things don’t relate to work and don’t reflect well on you, there’s no need for your boss to know about them.

2. Follow Your Boss’ Lead

When it comes to casual conversations with your boss, follow her lead. Not every conversation has to be about work; in fact, you probably don’t want it to be that way. It’s great to be able to talk to your supervisor casually about things other than spreadsheets and client deliverables, but developing a strong rapport means venturing off professional topic too. When those side conversations pop up, let your manager pick the topic—at least initially. Once you’ve established that going off on non-work related tangents is OK from time to time, you can then decide to strike up conversation on the TV show you’re binging or the new restaurant you tried over the weekend.

3. Know Your Triggers and Your Limits

Everyone has things that push him over the edge—pet peeves, personal insecurities, workplace drama. But before you blow off steam in front of your calm and collected manager, take a deep breath and, if necessary, excuse yourself for a couple of minutes to recollect yourself. Losing your cool or misfiring your emotions rarely goes over well, and if you act in haste you’ll likely be holding your head in your hands later on when you realize how easily your bitch session could’ve been avoided.

Being aware of your limits is right up there with knowing what triggers you. Ask yourself honestly how many glasses of wine you can consume before you become a person you’re not so interested in your boss seeing, or before you find it difficult to stick to the topics you’ve decided are kosher for sharing with your boss.

4. Don’t Share Anything You Wouldn’t Want Him to Remember

It’s tempting to share your views when the conversation is in full swing and your boss is sharing his frustrations about what’s going wrong with the company. Keep in mind that your boss will continue to be in a position of power long after he’s stopped being irritated. If you’ll be sorry you said it when he gets back to loving the company with all his heart, save your venting for your mom instead. Remember that active listening can be just as engaging as sharing your own views—not to mention it leaves you with far fewer causes for nightmares.

While nobody expects you to be perfect, the old less-is-more adage works quite well when it comes to being friends with your boss. She evaluates your work, and makes decisions about your compensation, workload, and promotion status. There’s no need to be aloof and pretend like you don’t have a life outside the office, but it’s important to keep the relationship dynamic in mind.

Photo of woman talking to her boss courtesy of Westend61/Getty Images.

Lauren Laitin is the Founder and Principal of ParachuteCoaching.com, an executive coaching practice, focused on helping professionals find fulfillment, stimulation, boundaries, and happiness at work and at home. After years of practicing law, Lauren has found her true passion and loves working with individuals, groups, and organizations to find theirs! Lauren lives in Washington, DC with her awesome husband and two fabulous daughters. Lauren loves to share helpful hints for career happiness. Find Lauren on Twitter @LaurenLaitin.

Meet The Author

Lauren Laitin is the Founder and Principal of ParachuteCoaching.com, an executive coaching practice, focused on helping professionals find fulfillment, stimulation, boundaries, and happiness at work and at home. After years of practicing law, Lauren has found her true passion and loves working with individuals, groups, and organizations to find theirs! Lauren lives in Washington, DC with her awesome husband and two fabulous daughters. Lauren loves to share helpful hints for career happiness. Find Lauren on Twitter @LaurenLaitin.